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【结 构 式】

【分子编号】19833

【品名】tert-butyl (2S)-1-[[(6S)-1-(3,5-dibromobenzyl)-5-(2,2-diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-6-yl]carbonyl]-2-pyrrolidinecarboxylate

【CA登记号】

【 分 子 式 】C37H38Br2N4O4

【 分 子 量 】762.54128

【元素组成】C 58.28% H 5.02% Br 20.96% N 7.35% O 8.39%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

The reaction of 3-phenacyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6(S)-carboxylic acid methyl ester (I) with 2,2-diphenylacetic acid (II) gives 5-(2,2-diphenylacetyl)-3-phenacyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6(S)-carboxylic acid methyl ester (III), which is condensed with 3,5-dibromobenzyl bromide (IV) in acetic acid yielding the corresponding 1-(3,5-dibromobenzyl) derivative (V). The hydrolysis of the ester group of (V) with NaOH affords the expected free acid (VI), which is condensed with L-proline tert-butyl ester (VII) giving the corresponding N-substituted L-proline ester (VIII). Finall this compound is coupled with phenylboronic acid (IX), catalized with palladium tetrakis(triphenylphosphine) complex.

1 Kim, D.; et al.; Non-peptide ligands of the human C5a receptor: Structure-activity relationship of a series of tetrahydroimidazopyridines. 213th ACS Natl Meet (April 13-17, San Francisco) 1997, Abst MEDI 088.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 19826 methyl (6S)-3-(2-oxo-2-phenylethyl)-3a,4,5,6,7,7a-hexahydro-3H-imidazo[4,5-c]pyridine-6-carboxylate C16H19N3O3 详情 详情
(II) 19827 2,2-diphenylacetic acid 117-34-0 C14H12O2 详情 详情
(III) 19828 methyl (6S)-5-(2,2-diphenylacetyl)-3-(2-oxo-2-phenylethyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylate C30H27N3O4 详情 详情
(IV) 19829 1,3-dibromo-5-(bromomethyl)benzene 56908-88-4 C7H5Br3 详情 详情
(V) 19830 methyl (6S)-1-(3,5-dibromobenzyl)-5-(2,2-diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylate C29H25Br2N3O3 详情 详情
(VI) 19831 (6S)-1-(3,5-dibromobenzyl)-5-(2,2-diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid C28H23Br2N3O3 详情 详情
(VII) 19832 tert-butyl (2S)-2-pyrrolidinecarboxylate C9H17NO2 详情 详情
(VIII) 19833 tert-butyl (2S)-1-[[(6S)-1-(3,5-dibromobenzyl)-5-(2,2-diphenylacetyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridin-6-yl]carbonyl]-2-pyrrolidinecarboxylate C37H38Br2N4O4 详情 详情
(IX) 16593 Phenylboronic acid;Benzeneboronic acid;Phenylboron dihydroxide 98-80-6 C6H7BO2 详情 详情
Extended Information